303 Life Lessons We All Learn But Keep Forgetting Cover

303 Life Lessons We All Learn But Keep Forgetting

I used to think beyond 7th grade math is only useful for physicists and statisticians. After the rule of three, which allows you to calculate discounts on prices, diminishing returns start to kick in fast.

I’ve remedied that view a bit; geometry and calculus have led to some of histories strongest philosophical insights, but I still like to imagine a world in which our high school table of subjects includes:

  • Human behavior.
  • Relationships.
  • Communication.
  • Body language.
  • Personal finance.
  • Etiquette.
  • Career discovery.
  • Work habits.
  • Creativity.

Until that happens, however, I’m grateful for people like Alexander J.A Cortes, who compile the curriculum of such a school of life for us to learn it now, as adults. On February 25th, he shared a tweet storm previewing his next book titled Untaught Truths of Adulthood, which went viral.

As I read through his nearly 100-tweet-long outpour of life lessons, many examples from my own life popped up in my mind. It’s only natural, for all of us learn many of these things, but we never articulate them. I reached out to him and asked whether he’d be up for a collaboration: The result is his treasure trove in long-form, with my experiences as backup to his insights.

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Why Losers Will One Day Rule The World Cover

Why Losers Will One Day Rule The World

“If you’re not a genius, don’t bother.”

Jim Bennett’s voice roars across the lecture hall.

“If you take away nothing else from my class, from this experience, let it be this. The world needs plenty of electricians, and a lot of them are happy.”

Portrayed by Mark Wahlberg in a 2014 rendition of The Gambler, Bennett is an English literature professor at UCLA. Or at least, he pretends to be. What he really teaches, however, is something else entirely.

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Trust in a World Full of Hidden Agendas Cover

Trust in a World Full of Hidden Agendas

In June 2017, fundraising for blockchain startups via so-called initial coin offerings, or ICOs, exploded to over $450 million and has since stayed there, on average.

The crypto space is new and unregulated, so collecting funds from retail investors via direct contributions is fast, easy, and profitable. Whenever money comes in these three flavors, scams are an immediate side effect.

Websites, white papers and roadmaps can be pulled out of thin air, so many have. Confido, Prodeum and LoopX are just a few of the projects that disappeared with millions of people’s dollars and even legit projects, like Tezos, can get stuck in frozen funds hell.

But the most interesting ICO of 2017 was neither a scam, nor did it promise a great future.

In fact, it was a completely useless project. Literally.

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Move Slower: How To Deal With the Fastness of Life Cover

Move Slower: How To Deal With the Fastness of Life

In investing, there’s this idea of a backdoor play.

For example, in 2014, Facebook announced it was going to use satellites, drones, and lasers, to bring the internet to the unconnected. Now, instead of buying Facebook stock and hoping they would succeed, you could’ve tried to figure out who they’d get the equipment from and buy their stock. Because even if Facebook failed, they’d purchase a lot of parts in the process.

In that sense, one of the best backdoor plays on cryptocurrencies must have been Twitter. The stock is up 100% year to date, partly because the platform dominates the crypto discussion.

While there is a lot of noise around this heated topic, a few clear voices stand out. Like Luke Martin, who’s amassed close to 150,000 followers in less than 8 months. One of Luke’s core ideas is to move slower with your investments.

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How To Make Better Decisions

In 1970, economist George Akerlof published a paper called The Market for Lemons: Quality Uncertainty and the Market Mechanism, in which he described an idea that would keep researchers busy for decades: adverse selection.

The concept describes a type of market inefficiency. When buyers and sellers have different information about the goods or services being sold, whichever party knows more can dictate the outcome of the transaction.

For example, sellers of used cars know whether their vehicle is of good quality or breaks down every ten miles, (a so-called ‘lemon’) but potential buyers don’t. As a result, sellers overcharge. Akerlof dubbed this phenomenon ‘asymmetric information’ and predicted a market death spiral in which, theoretically, no one would want to buy a car.

Of course the real used car market is very much alive, however inefficient. While measures to mitigate information asymmetry have been introduced, such as extended guarantees, inspections, and certifications, people still get ripped off every day.

But why? Akerlof received the Nobel prize in economics for his discovery and today, almost 50 years later, every US state has its own variant of the ‘Lemon law’ to protect consumers. Yet, we still make bad decisions, not just in purchasing goods, but everywhere.

And we really have no excuse to.

Avoidance Is Expensive

There are two types of capitalism: the kind that solves real problems and the kind that peddles placebos. The latter thrives on information asymmetry. In fact, it’s the only reason it works.

While con artists and scammers have been around for millennia, they’ve had to be a lot more creative since the rise of the internet. The wide dissemination of information at no cost has shrunk the gap a lot. Or rather, it’s increased how much we can shrink it ourselves. What used to be mostly a game of luck has now become a game of effort, but we avoid it just the same.

Take this picture of a turtle, for example.

It’s beautiful, isn’t it? While it’s a fantastic way to elicit emotions and get you to daydream about your next vacation, you don’t know where I took it from. But you could find out, thanks to Google Image Search.

With some more effort, you could even determine what kind of camera was used, where it was taken, who the photographer was, and ask them for more details. The question is, if I used this picture to try and sell you an all-inclusive trip to the Bahamas, would you?

Most of us don’t. We’re happy to comply when others prompt us to make decisions with as little context as possible. We form opinions based on headlines, pass judgements after reading tweets, and glance at pictures without demanding the frame they came in.

That’s what information asymmetry is at its core. A lack of context. It’s baffling how often we choose to decide under its influence, despite having all the tools we need to fight it.

Here are three that help you define, set, and leverage context to improve every single one of your decisions.

1. Knowing What You Know

One of Warren Buffett’s most popular mental models is the circle of competence. In a 2017 documentary, he describes it as follows:

“I can look at a thousand different companies and I don’t have to be right on every one of them, or even 50 of them. So I can pick the ball I want to hit. The trick in investing is just to sit there and watch pitch after pitch go by and wait for the one right in your sweet spot. And the people who are yelling ‘swing, you bum,’ ignore them.”

Knowing what you know increases the probability of your assumptions being right and thus helps you decide with confidence. Whatever lies outside of that circle is nothing but smoke and mirrors, but you can afford to ignore it, because you’re not going to take shots in the dark.

What’s remarkable is how small a circle we can get away with, yet still be successful. You could specialize in producing, selling, or investing only in tetracycline antibiotics, and that’d be more than enough to keep you busy for a lifetime.

To find the border of that circle early, we must walk to the edge, peer over, and maybe run a few low-risk experiments. But once we’ve set the perimeter, we can build a huge web of context inside it, while ignoring all the noise on the outside.

2. Knowing What You Don’t Know

In video games, it’s very common for the map of the terrain to be unknown when you start playing. Only as you move around do you uncover patches of the area, which then slowly begin to form a complete picture.

No matter how many black spots are left, keeping track of where they are allows you to shine your proverbial flashlight on them later, but not go there before you’re ready. There’s lots of smoke outside your circle, but that too is finite, at least for any particular decision. Knowing that boundary has value.

The more you optimize your life, the less you’ll have to step outside your circle of competence, but sometimes, life forces you to. It’s impossible to pick the perfect job when completely switching career fields, but being aware of how little you know, you can consult with experts, steer clear of big responsibilities at first, and prioritize what you’ll learn.

Even saying “I don’t know” out loud provides relief, makes it easier for others to empathize, and is more often seen as a sign of professionalism, rather than weakness.

3. Knowing How Much You Need To Know

Once you’ve determined where your wisdom ends and how much there is to attain for your specific decision altogether, another question presents itself, and it makes all the difference: how big is the gap between the two?

Former Secretary of State Colin Powell placed the ideal amount of information needed to make an educated decision between 40% and 70% of the total that’s available. Ideally, he says, you’d always keep waiting for more context at less than 40%, but never procrastinate after you’ve got 70% of the data.

No two situations are alike and this isn’t a hard rule, but thinking about whether you can push the edges of your circle of competence, and how far you’d have to drive them to avoid complete failure, is worth your while.

For example, if a stranger passes you in the street and doesn’t return your smile, your gut might tell you “this person’s arrogant.” However, armed with nothing but their appearance, you clearly have less information than you need to make that call.

Similarly, spending two whole afternoons to decide which out of three $50 backpacks you buy might be overdoing it, especially if you make $50/hr or more.

These are oversimplified, but the principle stands. Don’t let perceived urgency pressure you into sub-par decisions. Ask, search, and wait for what you need to pick not just an option that will do, but the option that’ll do best in your circumstances.

The Diet of the Wise

When Warren Buffett first took an interest in financial markets, there was no internet, yet he chose to fight information asymmetry regardless. It surely must have been an uphill battle, reading all those books, complicated financial reports, and whatever else he could get his hands on.

Yet here we are, history’s entire knowledge at our fingertips, often failing to google, go beyond the headline, or read the blurb of a book, let alone the whole thing. We’re too lazy to read and too busy to think, when that’s the diet of the wise. Better yet, it’s close to free.

In a fully connected world, information is only as asymmetric as you allow it to be. You have all the tools you need. Use them to build context. Avoid environments that force your hand. Know what you don’t know. Resist the temptation to move too quickly.

If your good decisions compound, maybe we’ll read about you someday.

How Should 20-Somethings Spend Their Time?

One day, you will wake up and be 75 years old. It happens to all of us. We blink and life passes. The question is whether it passes us by.

When you do get up on that fateful morning, look in the mirror, and realize you’re not happy, or that you’ve wasted too much time, it’ll be because right now, you didn’t properly answer life’s three big questions.

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The Fastest Way to Become Smarter Cover

The Fastest Way to Become Smarter

Four monks decided to meditate silently without speaking for two weeks. They lit a candle as a symbol of their practice and began. By nightfall on the first day, the candle flickered and then went out.

The first monk said: “Oh, no! The candle is out.”

The second monk said: “We’re not supposed to talk!”

The third monk said: “Why must you two break the silence?”

The fourth monk laughed and said: “Ha! I’m the only one who didn’t speak.”


95% of all talking covers only two topics:

  • The person whose mouth is open.
  • Stuff that’s outside our control.

The first monk got distracted by an outside event and felt compelled to point it out. He could’ve just re-lit the candle.

The second monk reminded everyone of a rule that had already been broken. He could’ve just kept meditating.

The third monk vented his anger. He could’ve just stayed calm.

The fourth monk got carried away with his ego. He could’ve just enjoyed his success in silence.

What all four have in common is that they shared their thoughts without filtering them, none of which added anything to improve the situation. If there had been a fifth, wiser monk, here’s what he would have done: Remain silent and keep meditating.

In doing so, he would’ve shown each of the other four monks their shortcomings without a single word. The more you talk, the more likely you are to say something stupid. The less you talk, the more you can listen.

Listening leads to learning.

What’s more, when you’re not talking, you have time to observe the situation until you spot the moment when it’s actually important to say something. Only speak when what you say is likely to have a significant, positive impact, for wisdom is cultivated in silence.

The less you speak, the smarter you get. And, maybe not quite coincidentally, the smarter you get, the less you speak.

The Cat With Oddly Colored Eyes Cover

The Cat With Oddly Colored Eyes

The snowflakes turned into raindrops immediately. It was freezing, but at the height of 22 floors, they didn’t stand a chance against the wind, throwing them against the windows of the Public Library with the brute force of a jackhammer.

Only one of the 120 seats in the legal section was filled. Behind the blue light of a Macbook screen, a tall, blonde woman in her early thirties bit her nails. Marissa glanced at her watch. Quarter past ten, Christmas Eve. Just as she was about to close the laptop, a familiar sound stopped her mid-movement.

*Pling*

“Not now. Please. Do I check it? I can’t not check it. Oh god. Please. Not. Now.”

She opened the email.

“F*ck.”

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12 Ways Detachment Will Make You More Successful Cover

12 Ways Detachment Will Make You More Successful

Which option do you prefer?

  1. I flip a coin. Heads, you get $100,000. Tails, you get nothing.
  2. I give you $10,000.

Of course, like any sane person, you’d take the $10,000. But maybe that isn’t so sane at all. In economics, there is this idea of expected value. You multiply the probability of an event by the potential payoff and get how much return you can statistically expect.

In this example, option one has an expected value of $50,000. Option two has an expected value of $10,000. The $40,000 difference is called risk premium. If you’re willing to take on risk, you stand to gain a much larger reward.

The reason most people aren’t is that they spend their entire lives chasing certainty. No matter how big the reward is, their desperate need for security has determined every outcome before they’re even presented with a choice.

In a 1951 book called The Wisdom of Insecurity, Alan Watts talks about the benefits of not craving certainty so much:

“I call it the ‘backwards law.’ When you try to stay on the surface of the water, you sink; but when you try to sink, you float. When you hold your breath, you lose it — which immediately calls to mind an ancient and much neglected saying, ‘Whosoever would save his soul shall lose it.’”

Today, the world is more uncertain than ever before, which makes the skill Watts talks about — the ability to dance with insecurity — more valuable than it ever was.

The name of that skill is detachment.

It is the art of being okay when life sucks, because you’re removed from the expectation that it pans out a certain way. Detachment enables you to do great things.

Here are 12 ways you can use it to be more successful.

1. Detach Yourself From Your Goals

Think of your biggest goal. Now 10x the result. Feels scary, doesn’t it? But notice how you instantly approach reaching it differently? That’s because you can’t get a million dollars with the same thinking that’d get you $100,000.

Of course you don’t need either. When you detach yourself from your goals, you can swing for home runs instead of second base. Regardless of where you end up, you’ll have more to be proud of.

2. Detach Yourself From Knowledge

Another good thing about setting huge goals, then letting go, is that you won’t feel pressured to look smart in how you go about attaining them. You are now free to say the three most liberating words in the world: “I don’t know.”

Like a child, you can just look at the world, wonder, and try things.

3. Detach Yourself From People’s Opinions

Detachment also allows you to finally make use of the birth right you have never really dared to claim: it’s okay to say how you feel. Anywhere, any time.

When you’re removed from the imaginary pain of what other people think about you, you can always express your feelings. You’re not worried whether they will offend others, because that’s their problem, not yours.

4. Detach Yourself From Your Own Opinions

The only thing more damaging to our self-esteem than other people’s opinions are our own. But nowhere does it say you need to hold on to them.

Set your negative self-talk down in the middle of the room. Look at it. Okay. Can you just let it sit there? The same goes for what you learn. Billionaire Ray Dalio says it took the biggest crisis of his life to figure this out:

“Rather than thinking, ‘I’m right.’ I started to ask myself, ‘How do I know I’m right?’”

5. Detach Yourself From Today

The reason you don’t need to worry so much about being right is that you can always be right tomorrow. Heck, you can even contradict yourself. The world keeps turning. No matter if you have a great day or a shitty day.

When you don’t expect much from today, you can just do your work and watch what happens, because it’s as good as any work on the way to figuring out what you really want to do.

6. Detach Yourself From Tomorrow

That said, tomorrow’s a long way away. Who knows what’s going to happen? Chances are, it won’t be as bad as you think. Or as good as you’d like. Like Henry Ford said:

“You can’t build a reputation on what you are going to do.”  —  Henry Ford

What you do today needn’t change the world, but you better do something.

7. Detach Yourself From Yesterday

Just like we can’t know where we’ll be tomorrow, it makes little sense to look too much at where we were yesterday. What’s done is done, good or bad. The lesson?

Time doesn’t matter. It just is. And it passes either way. There’s never a good reason to worry about it.

Don’t stress over today. Don’t worry about tomorrow. Don’t blame yourself for yesterday. There’s only one place in which we can truly live, because everything happens there: the present.

8. Detach Yourself From Physical Discomfort

My great-grandpa delivered curtains — on a bike. He rode 30, 40, 50 miles a day sometimes. Meanwhile, we throw a tantrum when our eyeliner is off. Or we arrive sweating at the office.

Most of us sit and type and walk and maybe carry a shopping bag once in a while. Whatever physical pains you have, chances are, the 100 billion humans that have lived before you would not consider them pains at all.

Can you just let them pass? They’re going to pass.

9. Detach Yourself From Mental Discomfort

What’s even more uncomfortable than sweating in a meeting is knowing that you’re sweating in a meeting. That goes back, once again, to people’s opinions. But there’s other mental discomfort throughout the day.

Boring tasks, slow results, alluring distractions, perceived risk, complicated decisions, the list goes on. Our days are full of cognitive dissonance, which occurs when what we want conflicts with what we’ve got to do to get there.

Sitting with this discomfort, instead of hastily giving in to it, is a skill.

10. Detach Yourself From Greatness

In Germany, there’s a law that every homeowner must sweep the small stretch of sidewalk in front of their house. If everyone does it, the streets are clean. Life is like that.

When you’re not thinking about how great you are or how great you want to be, you can focus on taking care of your own shortcomings, rather than pointing out others’ and silently judging them in your mind.

Just keep sweeping.

11. Detach Yourself From Perfection

Take a look at all the aspects of life you want to master: love, money, work, family, friends, health, happiness. There are so many, of course you can’t tackle them all at once! No one can.

Once you accept that life has trade-offs and make them, rather than constantly trying to bypass the fact itself, it becomes a lot easier.

Chances are you can have anything, maybe even everything you want. Just not all at the same time.

12. Detach Yourself From Happiness

All of this might make it seem like detachment is a path towards happiness. It’s not. It’s a way of living life while you let happiness do its thing. Happiness comes and goes in cycles, like seasons. Always has, always will.

The trick is to not be devastated every time it’s not there.


Life is full of choices that resemble our example from the beginning. There’s nothing wrong with a little certainty. Sometimes, you have to take the secure path. But most of the time, we do it because it’s easy.

Every time we play it safe, we take a snapshot of our lives. We frame the status quo, but forever lose what might have been. If you do it too often, you end up with a lot of pictures that look awfully the same. A photocopy of a life, not the real thing.

Ironically, caring a little less helps you get more out of everything you care so much about. Detachment allows you to demand more and not settle.

Ask not for certainty, ask for the best. Detach yourself, then act accordingly.

You only get one life. Swing for the fences.

A Simple Plan to Win the Year Cover

A Simple Plan to Win the Year

There’s this pithy quote floating around the web that I really like:

In school, you’re taught a lesson and then given a test. In life, you’re given a test that teaches you a lesson.

The one thing I don’t like about it is that it makes it sound like you have to wait to be given the test either way. You don’t. You can decide to take your own test any day of the week and when you do, you’ll learn a lesson instantly.

At the end of 2015, I designed such a test for myself: Learn something from a new book every day, whether that’s a chapter, a full book, a summary, or tons of interviews, and then write about it. Every day for the next year. The day I made the decision I already learned the first lesson.

The New Year Starts Today

In Do The Work, Steven Pressfield writes:

“Don’t prepare. Begin. Remember, our enemy is not lack of preparation; it’s not the difficulty of the project or the state of the marketplace or the emptiness of our bank account.

The enemy is Resistance. The enemy is our chattering brain, which, if we give it so much as a nanosecond, will start producing excuses, alibis, transparent self-justifications, and a million reasons why we can’t/shouldn’t/won’t do what we know we need to do. Start before you’re ready.”

As I prepared the website I thought “why not start writing also? It’ll be like a rolling start in a car race.” More like flying.

A big part of why 92% of people fail their New Year’s resolutions is that they think the switch is magical if they flip it on January 1st. But the switch is never magical and you can flip it any day. You can start a new year any day of the year. You’re not a calendar.

When you do it in December, you can fail a lot before January 1st and you won’t need pseudo-motivation to start because you can just keep going.

An Ode to December

Ever since I learned that lesson, December has become my busiest month of the year. Not with business, but with thinking. “What goals make sense for the next year? How can I make them simpler? What can I do to start today?”

Here’s what I’ve come up with this year.

1. Set a Simple, Insane Goal

Talking about cryptocurrency investing with a successful friend, I asked him: “What’s a good goal for me next year?” Without knowing how much I have, he said: “One million dollars.”

He explained: “Look, last year, around Christmas, I set a completely utopian goal. Not because I need the money. Just because. And I completely destroyed it.”

¯\_(ツ)_/¯

The obvious but hard to practice thinking behind this is that you can’t get a result that’s ten times bigger without a radically different approach. While everyone’s clawing for 1,000 more followers, can you sweat behind the curtain until you’re good enough to pop up on Oprah?

The path to bigger goals is always harder, less straightforward and more people will think you’re crazy. But it’s also less crowded.

Higher risk, more return. Speaking of which.

2. Completely Detach Yourself From Your Goal

The shrug emoji above is actually quite important. The reason my friend was so comfortable in setting such an insane goal is that he knew he didn’t control even half of it.

“You just do the best you can with what you’ve got, you go all in and then you let go.” Sticking with the one million dollar example, he continued: “You’d need to put in 100k and 10x that. But even if you pull off the first part, 90% of the result is out of your control. That’s fine, but that’s what it is.”

If your first thought is “I want a million dollars,” then your second thought should be “I don’t need a million dollars.” Not now, not ever.

What I like about my friend’s line of thinking is that it doesn’t artificially try to increase the part I control. More control just means more work. If I let go I can aim higher while focusing on less. I’ll probably like where I end up regardless.

3. Put All Your Energy Into 2–3 Core Strengths

Once you’ve placed your target on the moon, you can return to earth, turn your back on it and start digging. For short- to mid-term projects it makes sense to break it all down into small packages. For long-term, life-changing, way-out-there goals, that’s just depressing.

Which activities, if you do them long enough, will get you there? Which of those are you good at? Where have you already built assets you can work with?

Pick 2–3 of your core strengths and find a way to funnel those into your goal. How can you spend more time doing them? What others can you let go? If you’re already going strong, you can just keep going. For me it’s writing, saving a big share of my income and investing that as best as I can.

That’s it. Often, you need to change less of your day-to-day than you think.

4. Let Things Fall By The Wayside

Since this approach is so simple, what exactly I write, how much of my income I save, where I invest it, and so on, are all secondary. As long as I do those things, I’ll eventually get there.

As someone who thrives on plans, this is hard to wrap my head around. “Oh, I don’t need an exact portfolio allocation right now? Right, I don’t.” Even if you can follow a rigid, step-by-step plan, chances are you’ll get bored of it halfway through. But besides robbing you of the fun, tunnel vision also blindsides you to new opportunities along the way.

If a faster train to your goal passes you at the 50% marker, you first need to see it in order to jump on. But even before that, you have to buy a ticket.

5. Start Before You’re Ready

You don’t feel ready now, do you? That means it’s as good a time as ever.

What’s your goal? Can you make it bigger? Let go? Which activities will get you there? How much minutiae can you get rid of?

Don’t wait for life to give you a test. Design your own. If not now, when ever? It’s a new year, after all. And it starts today.

“Only put off until tomorrow what you are willing to die having left undone.”  —  Pablo Picasso